It definitely takes practice.
It's sort of natural for me. This will sound goofy, but I played with Tonkas, Hot Wheels, and Legos a lot when I was a kid, and had many trailers. The mechanics of backing a trailer aren't hard for me to grasp.
For which way to turn the wheel, one trick is to visualize which way you want to back the trailer. If you want it to go right, then look at you steering wheel. You'll want to make the BOTTOM of the steering wheel go right (in other words, you will be turning the wheel left). The trick, then, is to know how much to turn, and when to start straightening the rig up, etc.
Here's a challenge. I have a trailer hitch on my 5er, and tow a boat behind it. Try backing both up. To back up just a trailer, the truck moves in the opposite direction. But to back up a second trailer, the truck moves opposite the first trailer, and the same direction as the second trailer. I learned how to do this as a crew chief in the Air Force. I worked on F-16s. When we put these in the hangars, we backed them in. And we used these big mules that had tires as tall as me, and had four wheel steering, like monster trucks. The tow bar we used connected to the hitch on the mule, and to the nose gear on the jet. It had two pivot points. . the tow bar would pivot on the hitch, and the nosegear would turn. so if you wanted the jet to go left, you would make the mule back to the left. It took practice, but became fairly simple.
I agree with going to a big field or parking lot and practice for a while. Get some cones and make a little course and see how you do.
Hope this helps!!
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Shane Oler
'01 2500 4X4, ETH/6 speed, ISSPRO Pyro (pre-turbo)and Boost Pillar mount, Dark Garnet/Camel, 4" exhaust, Grill gaurd and nerf bars, 20K Reese 5er hitch
Other: '70 Olds Vista Cruiser 455 (future resto project)
30' Sandpiper 5er Super Slide bunkhouse(about 10k lbs. )